Process for production of phenolic polymerizable compound having physiological activity

Abstract

A process for producing a phenolic polymerizable compound represented by formula (1) or (2); wherein X 1 -X 9 independently represent a hydrogen atom, a hydroxy group, a saturated or unsaturated linear or branched alkoxy group having 1-10 carbon atoms, or a saturated or unsaturated linear or branched alkyl group having 1-10 carbon atoms; Y represents a hydrogen atom, a hydroxy group, a saturated or unsaturated linear or branched alkoxy group having 1-10 carbon atoms, a saturated or unsaturated linear or branched alkyl group having 1-10 carbon atoms, or a group represented by formula (6); and Z represents a hydrogen atom or a group represented by formula (3), which is characterized by heating a 4-hydroxycinnamic acid compound in the presence of a metal salt.

1 . A process for producing a phenolic polymerizable compound represented by Formula (1): 
       
         
           
           
               
               
           
         
         wherein X 1 -X 9  represent a hydrogen atom, a hydroxy group, a saturated or unsaturated linear or branched alkoxy group having 1-10 carbon atoms, or a saturated or unsaturated linear or branched alkyl group having 1-10 carbon atoms;
 Y represents a hydrogen atom, a hydroxy group, a saturated or unsaturated linear or branched alkoxy group having 1-10 carbon atoms, a saturated or unsaturated linear or branched alkyl group having 1-10 carbon atoms, or a group represented by Formula (3): 
 
       
       
         
           
           
               
               
           
         
         wherein X 10  and X 11  represent a hydrogen atom, a hydroxy group, a saturated or unsaturated linear or branched alkoxy group having 1-10 carbon atoms, or a saturated or unsaturated linear or branched alkyl group having 1-10 carbon atoms; and
 Z represents a hydrogen atom or a group represented by Formula (3); 
 wherein X 1 -X 11  may be the same or different from one another), 
 the process which is characterized by heating 4-hydroxycinnamic acid compounds in the presence of a metal salt. 
 
       
     
     
         2 . The process according to  claim 1 , wherein the 4-hydroxycinnamic acid compounds are represented by the following formula (4): 
       
         
           
           
               
               
           
         
         wherein X 12  and X 13  represent a hydrogen atom, a hydroxy group, a saturated or unsaturated linear or branched alkoxy group having 1-10 carbon atoms, or a saturated or unsaturated linear or branched alkyl group having 1-10 carbon atoms, and X 12  and X 13  may be the same or different from each other. 
       
     
     
         3 . The process according to  claim 2 , wherein the 4-hydroxycinnamic acid compounds are one or more kinds of compounds selected from a group consisting of p-coumaric acid, ferulic acid, coffeic acid, sinapic acid, di-t-butyl hydroxycinnamic acid compound, and artepillin C. 
     
     
         4 . The process according to  claim 3 , wherein the phenolic polymerizable compound generated by heating p-coumaric acid in the presence of a metal salt is a compound represented by Formula (5): 
       
         
           
           
               
               
           
         
       
     
     
         5 . The process according to  claim 3 , wherein a phenolic polymerizable compound generated by heating coffeic acid in the presence of a metal salt is a compound represented by Formula (8): 
       
         
           
           
               
               
           
         
       
     
     
         6 . The process according to  claim 3 , wherein the phenolic polymerizable compound generated by heating ferulic acid in the presence of a metal salt is a compound represented by Formula (10): 
       
         
           
           
               
               
           
         
       
     
     
         7 . The process according to  claim 3 , wherein the phenolic polymerizable compound generated by heating sinapic acid in the presence of a metal salt is a compound represented by Formula (11): 
       
         
           
           
               
               
           
         
       
     
     
         8 . The process according to  claim 3 , wherein a phenolic polymerizable compound generated by heating coffeic acid and ferulic acid in the presence of a metal salt is a compound represented by Formula (12): 
       
         
           
           
               
               
           
         
       
     
     
         9 . The process according to  claim 3 , wherein the phenolic polymerizable compound generated by heating p-coumaric acid and ferulic acid in the presence of a metal salt is a compound represented by Formula (13): 
       
         
           
           
               
               
           
         
       
     
     
         10 . The process according to  claim 1 , comprising performing heat treatment at 90° C. to 150° C. 
     
     
         11 . An anticancer agent, comprising a phenolic polymerizable compound produced by the process according to  claim 1 . 
     
     
         12 . An anticancer agent to oral cancer, comprising a phenolic polymerizable compound produced by the process according to  claim 1 . 
     
     
         13 . A lipase inhibitor, comprising a phenolic polymerizable compound produced by the process according to  claim 1 . 
     
     
         14 . An anti-obesity agent, comprising a phenolic polymerizable compound produced by the process according to  claim 1 . 
     
     
         15 . A skin disease therapeutic agent, comprising a phenolic polymerizable compound produced by the process according to  claim 1 . 
     
     
         16 . A food, a pharmaceutical agent, a quasi-drug, or cosmetics, comprising a phenolic polymerizable compound produced by the process according to  claim 1 . 
     
     
         17 . A novel physiologically active phenolic polymerizable compound represented by Formula (7) or a pharmacologically permissible salt thereof: 
       
         
           
           
               
               
           
         
       
     
     
         18 . A novel physiologically active phenolic polymerizable compound represented by Formula (9) or a pharmacologically permissible salt thereof: 
       
         
           
           
               
               
           
         
       
     
     
         19 . A novel physiologically active phenolic polymerizable compound represented by Formula (11) or a pharmacologically permissible salt thereof: 
       
         
           
           
               
               
           
         
       
     
     
         20 . A novel physiologically active phenolic polymerizable compound represented by Formula (12) or a pharmacologically permissible salt thereof: 
       
         
           
           
               
               
           
         
       
     
     
         21 . A novel physiologically active phenolic polymerizable compound represented by Formula (13) or a pharmacologically permissible salt thereof: